Even as season winds to a close, these May events showcase Southwest Florida’s exuberant arts and culture offerings. In Fort Myers, ’80s rock takes center stage with a performance from Pat Benatar & Neil Giraldo at Barbara B. Mann Performing Arts Hall. In Naples, The Naples Players ends its first season in its new home with the comedic production The Hallelujah Girls and on Marco Island, the first ever Miami-meets-Marco cultural exchange at Marco Island Center for the Arts’ Miami to Marco exhibition marks huge strides for the region’s art scene. Add these events to your May calendar.
Through June 7
The Florida House at Marco Island Historical Museum
The exhibit pays homage to Marco Island’s 60th anniversary with interactive experiences and artifacts of the island’s modern history, dating to 1965, when the Mackle brothers transformed the island into a coastal retreat, with 72 ranch-style homes, marketed as an affordable slice of the Florida dream for Northern families. The exhibit traces the era with archival images, documents, publications and artifacts, along with an app that allows visitors to design and personalize their own Mackle home. Learn More
Through May 4
FineMark Women’s Pro Tennis Championship at Bonita Bay Club, Naples
One of only five annual Women’s U.S. Tennis Association (USTA) Pro Circuit tournaments in the country, this competition is where rising stars gain traction. The sport’s 250 top competitors vie for $100,000 in prize money on the newly renovated club’s 18 Har-Tru tennis courts. Learn More
May 1
The Chopiniana with Eric Lu at Artis—Naples
One of the world’s most exciting young pianists returns to Artis—Naples to bring Chopin’s music to life as part of the Grand Piano Series. Since his first Naples performance in 2018 (the same year he took first place in the prestigious Leeds International Piano Competition), Eric has showcased his mastery of the Polish composer’s romantic style with premiere institutions like London Symphony Orchestra. Learn More
May 2
Pat Benatar & Neil Giraldo at Barbara B. Mann Performing Arts Hall, Fort Myers
The 1980s bad girl of rock and her longtime collaborator and husband bring their signature brand of house-shaking vocals and musical artistry to Fort Myers—the only South Florida stop on their 2025 tour. The singer—just as powerful as she was during the release of her 1980 Grammy-winning album, Crimes of Passion—and her husband joined the Rock and Roll Hall of Fame ranks in 2022. Learn More
May 3
Kentucky Derby Extravaganza at Corkscrew Weddings & Winery, Estero
With the Kentucky Derby off to the races, hat-crested ladies and men in seersucker suits experience the sporting spectacle in Southwest Florida style—in lounge chairs with a drink in hand. Catering from Naples’ new culinary supergroup, The Rose House, meets elegant pours, craft brews and cocktails amid the venue’s lush grounds, where a competitive best-dressed contest exalts the dapper and darling. Learn More
May 3
Arches Cinco De Mayo, Fort Myers Beach
Restore Fort Myers Beach Arches, Inc. celebrates Hispanic culture with this alfresco, festival-style live music event. Mariachi, Tejano, country and rock acts take to the main stage, and Latin dance performances and a special appearance fromNational Wrestling Alliance masked wrestler “The Bounty Hunter” keep the party going. Complete with a shrimp cook-off, a Mexican market, a car show from local Rollin Low Car Club and games and giveaways, this event brings the community together to support the organization’s efforts to create a commemorative arch to replace the iconic Fort Myers Beach arches. Learn More
May 4
Dance Series: Complexions Contemporary Ballet at Artis—Naples
Once a creative home for professional ballerina and United Arts Collier CEO Elysia Dawn, the boutique New York dance collective has a reputation for attracting principal dancers to its innovative ranks. Co-founded by ballet phenom Desmond Richardson, Complexions joins Naples Philharmonic for a groundbreaking interpretation of French composer Maurice Ravel’s Boléro. Learn More
May 5 — July 1
Miami to Marco at Marco Island Center for the Arts
Marco Island Center for the Arts brings new heft to its programming with a first-ever collaboration with Miami’s Museum of Contemporary Art of the Americas (MoCA-Americas). Works by 15 Hispanic artists from the museum’s Rodríguez Collection—such as late Cuban Modernist Cundo Bermúdez—highlight the diverse perspectives and forms of expression defining contemporary art today. Learn More
May 5 — July 31
Latin Surrealism: An Arte Viva Exhibition at the Norris Center, Naples
Arte Viva—Collier County’s ongoing celebration of Latin American culture—continues its stellar programming with an exhibition of 2D local artworks, inspired by famed surrealists like Frida Kahlo and Salvador Dalí. On May 22, the artists gather for a public reception, offering insights into the works curated by United Arts Collier. Learn More
May 6-30
Closing Group Exhibition at Harmon-Meek Gallery, Naples
Gallery owner Juliana Meek’s curation showcases the gallery’s 25 represented artists, from Richard Segalman’s dreamy Naples beach scenes to bold new compositions from frequent local exhibitor Reynier Llanes. “He’s the artist I look forward to the most because he’s always active—definitely a rising star in the art world,” Juliana says. Learn More
May 7-25
The Hallelujah Girls at The Naples Players
Naples’ star community theater closes out its first season in the newly renovated Kizzie Theater with a laugh-out-loud comedy about life, death and the power of female friendship. Updated acoustic systems soar as a host of local actors bring the ladies of SPA-DEE-DAH!, an abandoned church-turned-day-spa in rural Georgia, to life. Learn More
May 9
Honoring Moms with Art and Fashion at Newman Art Gallery, Naples
Legacy meets style in this Mother’s Day celebration at the family-run Newman Art Gallery. Nikki Newman, daughter of the late artist and gallery namesake David Newman, curates a special exhibition, featuring works inspired by her mother Michèle—her father’s longtime muse. The evening pairs intimate paintings with a trunk show of handcrafted Italian eyewear by Naples designer Maurizio Gamba, whose MauriGamba collection offers moms a stylish keepsake. Learn More
May 9
13th Annual “Ding” Darling & Doc Ford’s Tarpon Tournament, Sanibel Island
Nine hours, no outside communication—just anglers and the open water. This yearly catch-and-release tarpon tournament, held at the site of the first recorded tarpon caught on rod and reel, sees fishers compete for the biggest catch, followed by an evening awards ceremony. Learn More
May 10
Victor Wainwright and the Train at Arts Bonita
An encore doesn’t usually last 45 minutes—unless you’re seeing Victor Wainwright and the Train. After last season’s performance left the crowd buzzing and refusing to let the night end, this Grammy-nominated blues band returns to Arts Bonita for another performance. The Savannah, Georgia native frontman’s boogie woogie style has been compared to ’60s bluesy jazz legend Dr. John. Learn More
May 14
Brit Floyd—Pink Floyd Tribute at Hertz Arena, Estero
Another return to the Golden Age of Rock ’n’ Roll comes with the Pink Floyd cover band’s 50th anniversary celebration of the iconic Wish You Were Here album. The international tour builds on the success of 2023’s 50 Years of Dark Side tour, which arrived at Hertz Arena in classic Pink Floyd fashion—a two-and-a-half-hour show filled with lasers, inflatables, theatrics and all the hits. Learn More
May 14-18
Fort Myers Film Festival
Fort Myers film buffs flock to cultural institutions throughout Lee County—from Downtown’s Sidney & Berne Davis Art Center to BIG ARTS Sanibel Island—for a taste of what’s new and now in the world of cinema. Now in its 15th year, the festival has built a reputation for highlighting experimental and avant-garde indie films to the big screen, supplementing viewings with insightful talkbacks from the actors, filmmakers and directors who brought the projects to life. Learn More
May 16 — June 1
Prodigal Son at The Studio Players, Naples
Typically known for their slapstick comedies and farcical productions, Naples’ rag-tag theater troupe, The Studio Players, are breaking new ground with a dramatic, one-act performance of Prodigal Son. The season-ending show is led by burgeoning local theater talent, Landon Libbey, who makes his debut with The Studio Players after dazzling audiences in The Naples Players’ productions of A Christmas Carol and 42nd Street last season. Learn More
May 16
Hauser at Hertz Arena, Estero
Croatian virtuoso Stjepan Hauser transforms classical cello into an arena-worthy spectacle, complete with pyrotechnics and rock-concert energy. The viral sensation bridges technical classical mastery with showmanship that’s earned him collaborations with Andrea Bocelli and Steven Tyler and tours with Elton John’s band. Learn More
May 14-18th
Journey through the Americas at multiple Southwest Florida locations
After years of preparation, Gulfshore Opera launches its first-ever band show series, bringing performances to five Southwest Florida cities. The company’s GO Divas and Latin Infusion ensemble showcase highly-trained local musicians blending traditional folk and soulful melodies with contemporary pop and rock influences from across the Americas. The tour features a special appearance by students from Gulfshore Opera’s after-school music program, highlighting performers from diverse backgrounds. Learn More
May 17
Wanda Sykes: Please & Thank You Tour at Barbara B. Mann Performing Arts Hall, Fort Myers
One of the funniest and most well-known names in comedy makes a local stop on her first major stand-up tour in six years. The veteran comedian, actress and TV producer tackles topics ranging from politics to parenting with biting wit and undeniable charm. Learn More
May 23 and 24
Two-Day, Large-Canvas Painting Workshop at Masterpeace, Naples
Masterpeace owner and sculptor Alina Rubio brings Naples painter Jessie Perez into her serene studio space for an intimate and introspective painting workshop. With guidance from the artistic duo, participants riffle through old art books for inspiration, experiment with new mediums and form their unique artistic process, creating larger-than-life works to take home. Learn More
May 29 — June 1
Fringe Fort Myers at Alliance for the Arts and Broadway Palm Dinner Theater
The inclusive and uncensored arts festival wades into uncertain waters with an unjuried selection of artistic performances, ranging from theatrical debuts to dance. Independent performers are chosen by a lottery system, ensuring a lineup filled with unexpected perspectives and unknown voices rising to the top. Learn More